Stewart taking a shot again at Saratoga

Trainer who has had luck with long shots enters 30-1 Chess Chief in Travers

Travers entrant Chess Chief relaxes in his stall Wednesday August 21, 2019 on the Oklahoma Training Center track in Saratoga Springs, N.Y. Photo Special to the Times Union by Skip Dickstein

Travers entrant Chess Chief relaxes in his stall and checks out his surroundings Wednesday August 21, 2019 on the Oklahoma Training Center track in Saratoga Springs, N.Y. Photo Special to the Times Union by Skip Dickstein

SARATOGA SPRINGS — The first question asked when Dallas Stewart answered his cellphone Wednesday morning, was this: Why are you running Chess Chief in the Travers?

After a little bit of a laugh, Stewart said, "I don't know," from Louisville, Ky.

Chess Chief is listed as 30-1 on the morning line. Two other horses, Scars Are Cool and Laughing Fox, are also 30-1 so they are the colts in the 12-horse field given the least chance of winning the Grade I, $1.25 million Travers.

First though, a little advice. Toss Stewart and his horse out at your own risk.

Historically, he has had some horses pop at big numbers in big races. Witness: In 2006, Stewart pulled off the biggest upset in the history of the Kentucky Oaks when Lemons Forever won the 132nd running of the race at the odds of 47-1.

In 2008, another Stewart horse, Macho Again, ran second behind Big Brown in the Preakness. His odds? 40-1.

There have been others. In back-to-back runnings of the Kentucky Derby, Stewart horses lit up the tote board. In 2013, his Golden Soul finished second at 34-1 behind Orb; the following year he did the same thing as Commanding Curve (37-1) beat everyone in the Run for the Roses except for California Chrome.

Of course, it doesn't happen every time.

In 2016, Stewart did not have the magic touch in the Belmont Stakes. He ran 55-1 Seeking the Soul and 65-1 Forever d'Oro. They finished second to last and last, respectively.

Here comes Stewart into the Travers and he is given no chance. Think that is going to deter the 59-year-old Stewart, who got his start working as an assistant to Hall of Famer D. Wayne Lukas? Think again.

"He is an improving colt, getting better all the time," Stewart said. "I mean, you've got to try. He has a tough hill to climb, but he's doing great."

Chess Chief has raced 10 times in his career and has just a maiden win. That came in March, in his fifth career start. And, in true Stewart fashion, the trainer swung for the fences in the next start. He sent him straight to the Grade II Blue Grass, one of the last major prep races for the Kentucky Derby.

And he hit a single. Chess Chief, sent off at astronomical odds of 85-1, did not embarrass himself, finishing fifth. Among those he beat that day in Lexington was Sir Winston, who would go on to win the Belmont Stakes.

Since then, Chess Chief has raced four times and the average odds have been 31-1.

In his most recent race, Chess Chief went off at 35-1 in the Grade III West Virginia Derby and finished a credible second, beaten six lengths by the well-regarded Mr. Money.

"Mr. Money is a good horse and he's not in here," Stewart said.

It also doesn't hurt that Stewart has enlisted the services of Hall of Fame jockey Mike Smith, who has won the Travers four times, including back-to-back runnings with Arrogate in 2016 and West Coast the following year.

Chess Chief won't be a horse people are talking about in the days leading up to the Travers. Stewart can only hope the day after the race that everyone is talking about him.

The last race, the West Virginia Derby, was 1 1/8 miles and Chess Chief was making up ground. This will be the first time the son of Into Mischief tries 1 1/4 miles. Stewart thinks it will suit his horse; he also thinks there is enough early speed signed up for the race to give his horse a puncher's chance to make a run here.

""We just want to give him a shot," Stewart said. "It's a great race. Maybe we have a shot in here."